Dr. Aaron M. Hartel

Research Group

Department of Chemistry, Winthrop University

Rock Hill, SC 29733

 

 

Phone:              (803) 323-4942

Fax:                  (803) 323-2246

Office:              314B Sims

Lab:                 304 Sims

Email:               hartela@winthrop.edu  

 

 

 

Research Interests:

Organic Methodology. The development of new reactions is extremely important, particularly in drug discovery and the manufacture of pharmaceuticals. We are specifically interested in the application of organosilicon reagents in organic synthesis. Our current research focuses on the use of organosilylmetallic reagents and rearrangements involving migration of silicon directed toward the development of new synthetic organic methods. We have already developed a method for preparing β-hydroxyketones (aldols) by the selective α-reduction of α,β-epoxyketones using silyllithium reagents.

 

 

            We are also developing methods for the regio- and stereoselective preparation of simple and functionalized silyl enol ethers.

 

 

 

Chemical Education. We are also interested in developing new experiments which can be incorporated into undergraduate laboratory courses. We recently created an experiment for our second semester organic laboratory course (CHEM 304) in which commercial aspirin tablets are converted to Oil of Wintergreen. We are also developing a short synthesis of nicotine for our advanced synthesis laboratory course (CHEM 570).

 

 

We have also developed a short synthesis of nicotine from niacin.  The eight step route utilizes a balance of “sophomore” organic chemistry such as Grignard addition and hydrogenation and more advanced reactions like ring closing metathesis (RCM).  The synthesis was developed for use in our advanced synthesis laboratory course (CHEM 570).

 

 

 

 

Current Group Members:

Heather K Baker (2009)

Andre Merg (2010)

Brad D. Robertson (2008)        -           will be a graduate student at Duke University (Organic Chemistry)

           

 

 

Former Group Members:

            Sarah E. Wengryniuk (2007)    -           currently a graduate student at Duke University (Organic Chemistry)

Samantha C. Reynolds (2007)  -           currently a graduate student at Dartmouth College (Organic Chemistry)

W. Tyler Walker (2006)           -           currently a graduate student at Virginia Commonwealth University (Forensics)

Kristen Leadbetter (2005)        -           currently a graduate student at Winthrop University (Biology)

 

 

 

Group Publications:

“Preparation of Silyl Enol Ethers from Acyloin Derivatives Using Silyllithium Reagents,” Robertson, B. D.; Hartel, A. M. Tetrahedron Lett. 2008, 49, 2088-2090.

 

“Selective α-Reduction of α,β-Epoxyketones Using Silyllithium Reagents,” Reynolds, S. C.; Wengryniuk, S. E.; Hartel, A. M. Tetrahedron Lett. 2007, 48, 6751-6753.

 

 

 

Group Presentations at National Meetings:

“Preparation of Silyl Enol Ethers from Acyloin Derivatives Using Silyllithium Reagents,” Robertson, B. D.; Hartel, A. M., 235th ACS National Meeting, New Orleans, LA 2008 CHED-5.

 

“Formation of β-Hydroxy Silyl Enol Ethers from α,β-Epoxyketones Using Silyllithium Reagents.” Baker, H. K.; Hartel, A. M., 235th ACS National Meeting, New Orleans, LA 2008 CHED-5.

 

“Optimization of the Selective Reduction of α,β-Epoxycarbonyls with Silyllithium Reagents.” Wengryniuk S. E.; Hartel, A. M., 234th ACS National Meeting, Boston, MA 2007 WCC-5.

 

“Optimization of the Selective Reduction of α,β-Epoxycarbonyls with Silyllithium Reagents.” Wengryniuk S. E.; Hartel, A. M., 21st National Conference on Undergraduate Research, San Rafael CA 2007.

 

“Optimization of the Selective Reduction of α,β-Epoxycarbonyls with Silyllithium Reagents.” Wengryniuk S. E.; Hartel, A. M., 232nd ACS National Meeting, San Francisco, CA 2006 CHED-313.

 

 “Selective α-Reduction of α,β-Epoxycarbonyls with Silyllithium Reagents.” Reynolds, S. C.; Hartel, A. M., 232nd ACS National Meeting, San Francisco, CA 2006 CHED-315.

 

“Preparation of Methyl Salicylate from Commercial Aspirin Tablets: Two Experiments Highlighting Acid Catalyzed Acyl Substitution.” Hartel, A. M. 230th ACS National Meeting, Washington, DC, 2005. CHED-072.

 

 

 

Group Awards:

Aaron M. Hartel                       -           Joe B. Davis Award for Outstanding Teaching and Service (2007)

Samantha C. Reynolds              -           ACS Carolina-Piedmont Section Outstanding Scholastic Achievement Award (2007)

            Sarah E. Wengryniuk                -           Merck Index Women in Chemistry Scholarship (2007)

 

 

 

Photos from National ACS Meetings:

 

San Francisco, September 2006

 

                               

Sarah at her poster.                                                                              Samantha at her poster.

 

 

                               

Sarah talking to a professor from UGA.                                                Samantha gets lots of interested traffic, too.

 

 

                               

Sea lions at the wharfs.                                                                         Dr. Hartel at the bay.

 

 

                               

The beach at the Pacific Ocean.                                                            Alcatraz viewed from the wharfs.

 

 

 

Boston, August 2007

 

                               

Sarah is beside herself at the Merck kiosk.                                            Sarah presenting for the Merck Award.

 

 

 

New Orleans, April 2008

 

                        

Brad at his poster.                                                                                Heather at her poster.